KR840008323A - Method for preparing 5-acyl-2- (1H) -pyridinone - Google Patents

Method for preparing 5-acyl-2- (1H) -pyridinone Download PDF

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KR840008323A
KR840008323A KR1019840002298A KR840002298A KR840008323A KR 840008323 A KR840008323 A KR 840008323A KR 1019840002298 A KR1019840002298 A KR 1019840002298A KR 840002298 A KR840002298 A KR 840002298A KR 840008323 A KR840008323 A KR 840008323A
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South Korea
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hydrogen
cyano
ethyl
methyl
phenyl
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KR1019840002298A
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Korean (ko)
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KR900005011B1 (en
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디. 존슨(외 2) 윅톤
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가리디. 스트리트
메렐다우 파마 슈티칼스 인코포레이티드
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C07D213/85—Nitriles in position 3
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

내용 없음.No content.

Description

5-아실-2-(1H)-피리디논의 제조방법Method for preparing 5-acyl-2- (1H) -pyridinone

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (10)

1-R5-3-R6-2-(1-디메틸아미노-1-R4-메틸리데닐)-1,3-프로판디온을 표준 축합반응 조건에 따라 적절한 R3-치환된 아세토 아세트아미드와 반응시킴을 포함하여 일반식(Ⅰ)의 화합물 및 이의 약제학적으로 허용되는 염을 제조하는 방법. 1-R 5 -3-R 6 -2- (1- dimethylamino-R 4 -1-methyl Li denil) along the appropriate R-1,3-propanedione to standard condensation reaction conditions, 3-substituted acetoacetamide A process for preparing a compound of formula (I) and a pharmaceutically acceptable salt thereof, including reacting with a. 상기 식에서, R3는 H, -C≡N, NH2,CONH2또는 COOR(여기에서 R은 수소 또는 저급알킬임)이고, R4는 수소 또는 저급알킬이며, R5는 페닐, X-치환된 페닐, 피리딜, 티에닐, 푸릴, 피롤릴 또는 CR (여기에서 R은 하이드록시 또는 저급알콕시이고, X는 저급알킬, 저급알콕시, 저급알킬티오, 할로겐, 니트로, 저급알카노일, 알콕시카보닐, 카복시, 시아노, NH2, CONH2, 아미디노, 이디다졸-2-일 또는 CF3이다)이고, R6는 수소, 메틸, 에틸 또는 R5이다.Wherein R 3 is H, —C≡N, NH 2 , CONH 2 or COOR, where R is hydrogen or lower alkyl, R 4 is hydrogen or lower alkyl, R 5 is phenyl, X-substituted Phenyl, pyridyl, thienyl, furyl, pyrrolyl or CR, wherein R is hydroxy or lower alkoxy, X is lower alkyl, lower alkoxy, lower alkylthio, halogen, nitro, lower alkanoyl, alkoxycarbonyl , Carboxy, cyano, NH 2 , CONH 2 , amidino, imidazol-2-yl or CF 3 ), and R 6 is hydrogen, methyl, ethyl or R 5 . 제1항에 있어서, R3가 시아노인 방법.The method of claim 1, wherein R 3 is cyano. 제2항에 있어서, R5가 페닐인 방법.The method of claim 2, wherein R 5 is phenyl. 제3항에 있어서, R6가 메틸인 방법.The method of claim 3, wherein R 6 is methyl. 제3항에 있어서, R6가 에틸인 방법.The method of claim 3, wherein R 6 is ethyl. 제2항에 있어서, R5가 4-저급알킬티오 페닐인 방법.The method of claim 2, wherein R 5 is 4-lower alkylthio phenyl. 제1항에 있어서, R3는 시아노, R4는 수소, R5는 피리딜이고 R6는 에틸인 방법.The method of claim 1, wherein R 3 is cyano, R 4 is hydrogen, R 5 is pyridyl and R 6 is ethyl. 제1항에 있어서, R3는 시아노, R4는 수소, R5는 티에닐이고, R6는 메틸인 방법.The method of claim 1, wherein R 3 is cyano, R 4 is hydrogen, R 5 is thienyl, and R 6 is methyl. 제1항에 있어서, R3는 시아노, R4는 수소, R5는 푸릴이고, R6는 에틸인 방법.The method of claim 1, wherein R 3 is cyano, R 4 is hydrogen, R 5 is furyl, and R 6 is ethyl. 제1항에 있어서, 반응생성 혼합물을 섬광크로마토그라피법을 이용하여 분리시키는 방법.The method of claim 1, wherein the reaction mixture is separated by flash chromatography. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019840002298A 1983-04-29 1984-04-28 5-acyl-2-(1h)-pyridinones and preparing process thereof KR900005011B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US06/490,081 US4568751A (en) 1983-04-29 1983-04-29 5-Acyl-2-(1H)-pyridinones
US490081 1983-04-29
US490,081 1990-03-07

Publications (2)

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KR840008323A true KR840008323A (en) 1984-12-14
KR900005011B1 KR900005011B1 (en) 1990-07-16

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KR1019840002298A KR900005011B1 (en) 1983-04-29 1984-04-28 5-acyl-2-(1h)-pyridinones and preparing process thereof

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US (1) US4568751A (en)
EP (2) EP0124089B1 (en)
JP (2) JPS59206356A (en)
KR (2) KR900005010B1 (en)
AR (1) AR240313A1 (en)
AT (2) ATE25678T1 (en)
AU (2) AU557543B2 (en)
CA (2) CA1242443A (en)
DD (1) DD223444A5 (en)
DE (2) DE3462503D1 (en)
DK (2) DK159425C (en)
ES (2) ES8505955A1 (en)
GR (2) GR81967B (en)
HU (2) HU191753B (en)
IE (2) IE57285B1 (en)
IL (2) IL71649A (en)
NO (2) NO164416C (en)
NZ (2) NZ207960A (en)
PH (1) PH20256A (en)
PT (2) PT78493B (en)
SU (1) SU1299505A3 (en)
ZA (2) ZA843034B (en)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5118696A (en) * 1983-04-29 1992-06-02 Merrell Dow Pharmaceuticals Inc. 5-Acyl-2-(1H)-pyridinones useful for treating cardiac failure
US4731371A (en) * 1984-03-29 1988-03-15 Merrell Dow Pharmaceuticals Inc. Certain 5-acyl-1,2-dihydro-2-oxo-3-pyridinecarbonitriles which are useful as cardiotonic agents
US4992452A (en) * 1983-04-29 1991-02-12 Merrell Dow Pharmaceuticals Inc. Certain 5-acyl-2-(1H)-pyridinones useful in treating cardiac failure
US5428045A (en) * 1983-04-29 1995-06-27 Merrell Dow Pharmaceuticals Inc. 5-acyl-2-(1H)-pyridinoes
US4568751A (en) * 1983-04-29 1986-02-04 Merrell Dow Pharmaceuticals Inc. 5-Acyl-2-(1H)-pyridinones
US4853395A (en) * 1983-04-29 1989-08-01 Merrell Dow Pharmaceuticals Inc. Certain 3-carboxylate or 3-carbamyl-5-acyl-2-(1H)-pyridinones having cardiotonic properties
US4732982A (en) * 1983-11-03 1988-03-22 Merrell Dow Pharmaceuticals Inc. Novel alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones
US5212314A (en) * 1983-11-03 1993-05-18 Merrell Dow Pharmaceuticals Inc. Alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones
US4657919A (en) * 1984-08-03 1987-04-14 E. I. Du Pont De Nemours & Co. Pyridone esters as inotropic agents
US4650806A (en) * 1985-01-14 1987-03-17 Sterling Drug Inc. Cardiotonic 5-(heterylcarbonyl)-pyridones

Family Cites Families (9)

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Publication number Priority date Publication date Assignee Title
DE2531035A1 (en) * 1975-07-11 1977-01-27 Basf Ag PROCESS FOR THE PRODUCTION OF 5-CYANPYRIDONE- (6)
US4072746A (en) * 1975-10-14 1978-02-07 Sterling Drug Inc. 3-Amino-5-(pyridinyl)-2(1H)-pyridinones
GB1596887A (en) * 1977-07-15 1981-09-03 Rohm & Haas 2-pyridone derivatives and their use as plant growth regulators
DE3005069A1 (en) * 1980-02-11 1981-08-20 Cassella Ag, 6000 Frankfurt 2-Oxo-6-hydroxy-1,2-di:hydro-pyridine-5- carboxylic acid derivs. - prepd. by reaction of alkoxy:methylene-malonate cpds. with substd. acetamide cpds.
DE3106460A1 (en) * 1980-03-03 1982-01-28 Sandoz-Patent-GmbH, 7850 Lörrach 2 (1H) -PYRIDINONE DERIVATIVES, THEIR PRODUCTION AND THE PHARMACEUTICAL PREPARATIONS CONTAINING THE SAME
US4412077A (en) * 1982-03-15 1983-10-25 Sterling Drug Inc. Process for preparing 5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinone
US4524149A (en) * 1982-03-15 1985-06-18 Sterling Drug Inc. 5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their cardiotonic use
US4568751A (en) * 1983-04-29 1986-02-04 Merrell Dow Pharmaceuticals Inc. 5-Acyl-2-(1H)-pyridinones
DE3406329A1 (en) * 1984-02-22 1985-08-22 Merck Patent Gmbh, 6100 Darmstadt PYRIDONE

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NO164415B (en) 1990-06-25
JPS59206355A (en) 1984-11-22
IL71649A (en) 1987-10-30
HU191928B (en) 1987-04-28
NO841691L (en) 1984-10-30
DD223444A5 (en) 1985-06-12
IE841047L (en) 1984-10-29
AU571219B2 (en) 1988-04-14
EP0124090B1 (en) 1987-04-01
NZ207960A (en) 1987-05-29
GR81967B (en) 1984-12-12
AU557543B2 (en) 1986-12-24
DK213584D0 (en) 1984-04-27
IL71648A0 (en) 1984-07-31
KR900005011B1 (en) 1990-07-16
DK159425C (en) 1991-03-18
PT78493B (en) 1986-05-20
IE841046L (en) 1984-10-29
NO164415C (en) 1990-10-03
DK213284D0 (en) 1984-04-27
IL71648A (en) 1987-11-30
DK159425B (en) 1990-10-15
NO841690L (en) 1984-10-30
EP0124089A1 (en) 1984-11-07
JPH0579668B2 (en) 1993-11-04
ATE26262T1 (en) 1987-04-15
GR81990B (en) 1984-12-12
US4568751A (en) 1986-02-04
PT78493A (en) 1984-05-01
DK159424C (en) 1991-03-18
ZA843033B (en) 1984-11-28
EP0124089B1 (en) 1987-03-04
KR900005010B1 (en) 1990-07-16
IE57273B1 (en) 1992-07-01
ES531911A0 (en) 1985-06-01
ES531910A0 (en) 1985-06-01
EP0124090A1 (en) 1984-11-07
DK213284A (en) 1984-10-30
AR240313A1 (en) 1990-03-30
DE3462503D1 (en) 1987-04-09
NO164416B (en) 1990-06-25
JPS59206356A (en) 1984-11-22
DE3462889D1 (en) 1987-05-07
CA1242443A (en) 1988-09-27
CA1256880A (en) 1989-07-04
ES8505956A1 (en) 1985-06-01
NZ207961A (en) 1986-09-10
HUT34007A (en) 1985-01-28
PT78491B (en) 1986-05-22
IE57285B1 (en) 1992-07-15
SU1299505A3 (en) 1987-03-23
DK159424B (en) 1990-10-15
PH20256A (en) 1986-11-14
ES8505955A1 (en) 1985-06-01
HUT34006A (en) 1985-01-28
KR840008322A (en) 1984-12-14
JPH058192B2 (en) 1993-02-01
PT78491A (en) 1984-05-01
DK213584A (en) 1984-10-30
AU2713184A (en) 1984-11-01
NO164416C (en) 1990-10-03
ZA843034B (en) 1984-11-28
HU191753B (en) 1987-04-28
IL71649A0 (en) 1984-07-31
AU2714184A (en) 1984-11-01
ATE25678T1 (en) 1987-03-15

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